Tetrahedron: Asymmetry

(1S, 2S, 7R, 8aS)-and (1S, 2S, 7S, 8aS)-trihydroxyoctahydroindolizine: Two new glycosidase inhibitors by nitrone cycloaddition strategy

A Goti, F Cardona, A Brandi, S Picasso, P Vogel

Index: Goti, Andrea; Cardona, Francesca; Brandi, Alberto; Picasso, Sylviane; Vogel, Pierre Tetrahedron Asymmetry, 1996 , vol. 7, # 6 p. 1659 - 1674

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Citation Number: 80

Abstract

The two new epimeric (1S, 2S, 7R, 8aS)-and (1S, 2S, 7S, 8aS)-1, 2, 7- trihydroxyoctahydroindolizines4 and 5 have been synthesized via methylenecyclopropane- nitrone cycloaddition-rearrangement methodology employing an enantiomerically pure l- tartaric acid derived nitrone 7b. Highly stereoselective reductions of the intermediate indolizidinone 10b and final deprotection furnished the two title indolizidinetriols 4 and 5, ...